The 17 Worst Celebrity Breakups of All Time

Relationships in Hollywood have always been under a microscope, with every date, argument, and cryptic social media post analyzed by millions. Unlike typical relationships, where breakups can happen in private, celebrity splits play out in headlines, courtrooms, and sometimes even diss tracks. The pressure of public scrutiny, relentless paparazzi, and fan speculation often amplify the drama, turning what might be a normal breakup into a full-blown media circus. Whether it’s a messy cheating scandal, a public war of words, or a subtle unfollow that sparks internet chaos, these relationships rarely end quietly.  

Over the past few decades, we’ve witnessed some of the wildest celebrity breakups—sometimes solely based on the internet’s ability to twist a story beyond recognition. Whether it’s an unexpected divorce, a love triangle that divides fans, or a breakup that spawns an entire album, Hollywood heartbreak is never simple. Even the biggest stars struggle with romance, proving that fame and fortune can't guarantee a happily ever after.

Keep scrolling to see, in no particular order, the messiest celebrity breakups of all time—perfect timing for anyone feeling pessimistic about love or anti-Valentine’s Day. 

Brad Pitt and Jennifer Aniston

Brad Pitt and Jennifer Aniston’s breakup in 2005 remains one of Hollywood’s most infamous splits. After five years of marriage, the couple announced their separation, but speculation quickly grew that Pitt had fallen for his Mr. & Mrs. Smith co-star, Angelina Jolie. Though Pitt and Jolie denied any wrongdoing at the time, their swift romance following the divorce fueled cheating rumors. Aniston was painted as America’s sweetheart and the heartbroken ex, while Jolie was labeled the "other woman." The love triangle became a media obsession, with fans taking sides for years. Even now, their breakup remains one of the most talked-about in celebrity history.

Machine Gun Kelly and Megan Fox

Machine Gun Kelly and Megan Fox's tumultuous relationship has been a rollercoaster of passionate declarations and public breakups, but their most recent and seemingly final split in 2024 took things to another level—especially with Fox reportedly pregnant with their child. The drama intensified when Fox revealed that she found something on MGK’s phone that was "unforgivable," though she refused to disclose exactly what it was. Fans have speculated everything from infidelity to deeper betrayals, but the mystery remains unsolved. While their relationship has always been unpredictable, this latest split feels definitive. As for what was on MGK’s phone? That may be one Hollywood secret that never gets uncovered.

Justin Timberlake and Britney Spears

Justin Timberlake and Britney Spears were pop royalty in the early 2000s, but their breakup was laced with drama—particularly thanks to Timberlake’s "Cry Me a River" music video, which heavily implied that Spears cheated. Spears mainly remained quiet about the split at the time. The media quickly ran with the narrative, painting Spears as the villain, and Timberlake capitalized on it throughout his solo career. Decades later, Spears revealed in her memoir The Woman in Me that their relationship was far more complicated than the public knew, sparking renewed criticism of Timberlake and proving that this messy breakup still has lasting effects.

John Mayer and Taylor Swift

Taylor Swift and John Mayer’s breakup in 2010 turned into one of the most infamous musical callouts in pop history. Their brief but intense romance reportedly ended on bad terms, with Swift releasing "Dear John," a scathing breakup ballad that painted Mayer as a manipulative heartbreaker. The song’s lyrics—especially lines about being “too young to be messed with”—suggested that their 12-year age gap played a role in the fallout. Mayer later claimed he was blindsided and called the song “humiliating,” but Swift never directly confirmed it was about him. Years later, fans reignited the drama when Swift re-released the track, proving that this messy breakup still lingers in pop culture.

Scott Disick and Kourtney Kardashian

Scott Disick and Kourtney Kardashian’s on-again, off-again relationship was a rollercoaster that played out over more than a decade—and much of it was captured on Keeping Up With the Kardashians. Their final split in 2015 came after years of Disick’s partying and alleged infidelities, with paparazzi photos of him cozying up to another woman being the final straw for Kardashian. Despite the messy breakup, the two remained co-parents to their three children, though tensions often flared, especially when Kardashian moved on with Travis Barker. Disick has openly expressed his struggles with the split, making this one of reality TV’s most dramatic breakups.

Justin Bieber and Selena Gomez

"Jelena" fans endured years of on-again, off-again drama, but the final split was the most chaotic. Not long after their last breakup, Justin Bieber quickly moved on from Selena Gomez with Hailey Baldwin, whom he married in 2018, Fans accused Bieber of overlapping relationships, while Gomez released "Lose You to Love Me," a song widely interpreted as a response to their breakup. Social media remains divided to this day, with constant speculation about hidden messages in songs and subtle shade thrown in interviews. 

Their past relationship was recently brought into conversation after cryptic posts on TikTok from Hailey Bieber seemed to be targeting Gomez, and Gomez responded to these rumors on her personal Instagram. The internet seems to be dedicated to fueling an ongoing frenzy here, despite Bieber being married to Hailey with a child and Gomez's recent engagement to Benny Blanco. 

Brad Pitt and Angelina Jolie

Dubbed "Brangelina," this power couple’s split was anything but amicable. After over a decade together, Angelina Jolie filed for divorce from Brad Pitt, citing "irreconcilable differences," but reports of an alleged altercation between Pitt and their son Maddox on a private jet fueled even more speculation. The divorce turned into a lengthy, bitter custody battle that was just recently resolved in 2025. And it's not just between the two ex-lovers: Many of Pitt's children are making an effort to drop his last name legally. 

Ariana Grande and Pete Davidson

A whirlwind romance that began with matching tattoos and an engagement within weeks ended just as dramatically. In Grande's album, Sweetener, she even titled a track after Davidson. However, not long after the release of this album, the two split. The breakup followed the tragic passing of Grande’s ex, Mac Miller, leading many to speculate that the emotional toll contributed to the split. Davidson later joked about the breakup in his stand-up sets, while Grande released thank u, next, solidifying the relationship’s place in pop culture history.

Tristan Thompson and Khloe Kardashian

Tristan Thompson and Khloé Kardashian’s relationship was plagued by repeated cheating scandals, making their breakup one of the most dramatic in reality TV history. The first major blow came in 2018 when Thompson was caught cheating just days before Kardashian gave birth to their daughter, True. Despite attempting to move past it, another scandal erupted in 2019 when he was exposed for kissing Kylie Jenner’s then-best friend, Jordyn Woods. While Kardashian gave him multiple chances, it was then revealed in 2021 that Thompson had fathered a child with another woman while secretly trying to reconcile with her. Their breakup became a media frenzy and evidence of how some relationships are doomed to repeat the same toxic cycle.

Jason Sudeikis and Olivia Wilde

Olivia Wilde and Jason Sudeikis’ breakup in 2020 seemed amicable at first—until rumors swirled about Wilde’s romance with Harry Styles. The timeline of their split became a hot topic, with speculation that Wilde and Styles, who met on the set of Don’t Worry Darling, started dating before she officially ended things with Sudeikis. The drama escalated when Wilde was publicly served custody papers from Sudeikis while on stage at CinemaCon, an embarrassing moment that fueled headlines. Later, their former nanny made bombshell claims about the breakup, alleging that Sudeikis was blindsided and even laid under Wilde’s car to stop her from leaving to see Styles. Though Wilde and Sudeikis denied the nanny’s allegations, their messy split—and the Harry Styles love triangle—became one of Hollywood’s most talked-about breakups of the moment.

Kanye West and Kim Kardashian

Kim Kardashian and Kanye West’s 2021 divorce quickly spiraled into one of the messiest celebrity breakups in recent history. While they initially cited “irreconcilable differences,” things took a dramatic turn when Kanye launched multiple public attacks on Kim and her then-boyfriend, Pete Davidson, via social media. From cryptic Instagram rants to disturbing music videos depicting violence against Davidson, Kanye’s erratic behavior kept their breakup in the headlines. Meanwhile, Kardashian remained primarily silent, focusing on co-parenting their four children. Despite finalizing their divorce in 2022, the drama hasn’t fully died down, proving that even the biggest power couples aren’t immune to messy endings.

Liam Hemsworth and Miley Cyrus

After a decade of breakups, makeups, and an on-and-off engagement, Miley Cyrus and Liam Hemsworth’s marriage lasted less than a year. While they kept their divorce reasons vague, Cyrus later released Flowers, a song fans believed was full of references to Hemsworth’s alleged infidelity. The track’s music video, filmed in a house rumored to have been a site of Hemsworth’s cheating, only fueled speculation that their breakup was messier than they let on.

Joe Jonas and Sophie Turner

Joe Jonas and Sophie Turner’s 2023 divorce shocked fans, but the drama that followed made it even messier. What started as a seemingly mutual split quickly turned sour when reports surfaced alleging that Turner’s party lifestyle clashed with Jonas’ more “responsible” parenting—claims many saw as a publicity move in Jonas’ favor. Turner fired back with a lawsuit, accusing Jonas of withholding their children’s passports to prevent them from returning to the UK with her. As social media took sides, insiders continued to leak conflicting narratives, making their breakup one of the most publicized and contentious celebrity divorces in recent years.

Ben Affleck and Jennifer Lopez

Ben Affleck and Jennifer Lopez’s 2004 breakup was one of the most talked-about splits of the early 2000s. Dubbed "Bennifer," the couple’s whirlwind romance, flashy engagement, and high-profile public appearances made them Hollywood’s ultimate power couple. However, intense media scrutiny and relentless paparazzi pressure reportedly took a toll on their relationship. Just days before their scheduled wedding, they postponed the ceremony due to "excessive media attention," and by early 2004, they officially called it quits. Lopez later admitted that Affleck was her “first big heartbreak.”

Nearly two decades later, in a shocking full-circle moment, the two rekindled their romance and married in 2022—just to end up breaking up again. What seemed like an on-again, off-again romance, it appears the two have officially split, but remain amicable. 

Matty Healy and Taylor Swift

Taylor Swift and Matty Healy’s decade-long, on-again, off-again situationship has been one of the most mysterious and chaotic entanglements in modern pop culture. First linked in the early 2010s, the two fueled romance rumors for years but never publicly confirmed their connection—until 2023, when they shocked the world by going fully public just weeks after Swift’s breakup with Joe Alwyn. Their whirlwind romance sparked intense debate and ended just as quickly as it began. But the real fallout came with Swift’s 2024 album The Tortured Poets Department, which fans believe is packed with references to their messy history, from cryptic lyrics about their past to brutal breakup anthems. Was it just a rebound, or something deeper? One thing’s for sure—this situationship left a mark on both music and pop culture.

Barry Keoghan and Sabrina Carpenter

Sabrina Carpenter and Barry Keoghan's short-lived romance had fans buzzing, but their 2024 breakup stirred even more speculation. The two first sparked dating rumors in late 2023, quickly becoming a favorite internet couple thanks to their unexpected yet intriguing dynamic. However, problems arose as Carpenter’s skyrocketing career and Keoghan’s demanding film schedule put a strain on their relationship. Then, rumors of Keoghan cheating on Carpenter with a TikTok influencer went viral in December 2024 (to the point where Keoghan took to Instagram to ask fans to stop speculating and be kind). Although he never denied or admitted to the cheating claims, this breakup seemed to be messier than we thought. 

Johnny Depp and Amber Heard

What started as a whirlwind romance turned into one of the most public and contentious celebrity divorces of all time. Amber Heard accused Johnny Depp of domestic abuse, leading to years of legal battles, defamation lawsuits, and viral court proceedings. The defamation case divided fans, with social media platforms becoming a battleground for heated debates and a place for conversation on the alleged and grotesque acts by Depp. The 2022 trial, which Depp won in the US, solidified this as one of the messiest breakups (and relationships) in recent times.